“Dehydroxyfluorination reaction” for replacing hydroxyl group of a hydroxyl group-containing compound with fluorine atom is an important reaction in syntheses of fluorine-containing organic compounds. The following are typical examples.
1) a process (Patent Publication 1 and Patent Publication 2) in which a substrate having a hydroxyl group is reacted with a perfluoroalkanesulfonyl fluoride, such as perfluorobutanesulfonyl fluoride, in the presence of a special, strongly basic, organic base, such as DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).
2) a process (Non-patent Publication 1) in which a substrate having a hydroxyl group is reacted with perfluorobutanesulfonyl fluoride in the presence of an organic base, such as triethylamine, and “a salt or complex comprising an organic base and hydrogen fluoride” such as triethylamine tris(hydrogen fluoride) complex.
3) a process (Patent Publications 3-6) for producing a fluoro derivative by reacting a specific hydroxy derivative with trifluoromethanesulfonyl fluoride in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride” (such as triethylamine tris(hydrogen fluoride) complex).
4) a process (Non-patent Publication 2) in which a hydroxyl group is converted into a fluorosulfate, followed by replacement with a fluorine anion.    Patent Publication 1: U.S. Pat. No. 5,760,255 specification    Patent Publication 2: U.S. Pat. No. 6,248,889 specification    Patent Publication 3: International Publication 2004/089968 Pamphlet (Japanese Patent Application Publication 2004-323518)    Patent Publication 4: Japanese Patent Application Publication 2006-083163    Patent Publication 5: Japanese Patent Application Publication 2005-336151    Patent Publication 6: Japanese Patent Application Publication 2006-008534    Non-patent Publication 1: Organic Letters (US), 2004, Vol. 6, No. 9, p. 1465-1468    Non-patent Publication 2: Tetrahedron Letters (UK), 1996, Vol. 37, No. 1, p. 17-20